Jesse Fifield

My 12-year real estate journey has taken me from Boston back to my home state of Maine, where I’ve been helping clients navigate everything from single-family homes to large-scale new developments. I got my start in rentals and property management, and that experience still shapes the way I guide clients—whether they’re buying, selling, or [...]

My 12-year real estate journey has taken me from Boston back to my home state of Maine, where I’ve been helping clients navigate everything from single-family homes to large-scale new developments. I got my start in rentals and property management, and that experience still shapes the way I guide clients—whether they’re buying, selling, or investing.

Before joining Portside, I spent a year and a half with one of Maine’s top brokerages by volume, gaining hands-on experience with new developments and learning the ins and outs of the local market. Now at Portside, I work as a team with my wife Emily, combining our strengths to serve clients throughout Maine, New Hampshire, and Massachusetts with a down-to-earth, team-first approach. We keep things simple, honest, and always focused on what’s best for our clients